Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Transcribed Image Text:**Question 20:**
For each of the following substrates, determine whether an SN1 process is likely to involve a carbocation rearrangement or not.
**Substrates:**
(a)
Structure: A tertiary alkyl iodide.
(b)
Structure: A secondary alcohol with branching that can lead to a tertiary carbocation upon rearrangement.
(c)
Structure: A secondary alcohol without branching that may lead to rearrangement.
(d)
Structure: A primary alcohol with branching present.
(e)
Structure: A secondary alkyl bromide that could lead to rearrangement to form a more stable carbocation.
(f)
Structure: Cyclohexyl chloride, where rearrangement is not typically possible.
**Explanation:**
- Substrates like (b), (c), and (e) are likely to involve rearrangement in an SN1 reaction, as the carbocation stability can be increased by shifting to form a more stable carbocation, such as tertiary from secondary.
- Substrate (a), being already tertiary, will not undergo rearrangement.
- Substrate (d), although primary, does not have a favorable pathway for rearrangement in the context of SN1.
- Substrate (f) is unlikely to undergo rearrangement since cyclohexyl structures typically do not rearrange.
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